Career Timeline of Charley Crockett: Major Achievements and Milestones

By Popular Timelines Editorial Team · Updated: October 26, 2025

How Charley Crockett built a successful career. Explore key moments that defined the journey.

Charley Crockett is a contemporary neotraditional country singer-songwriter from the United States. Active since 2015, he has released 15 studio albums, gaining increasing recognition. His albums 'The Man from Waco', '$10 Cowboy', 'Lonesome Drifter' and 'Dollar a Day' achieved commercial success, charting on the US Billboard 200 in 2022, 2024, and 2025. Crockett's work is notable for its blending of classic country sounds with modern sensibilities.

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Full Timeline Career & Achievements

2009: Busking in New York City

By 2009, Charley Crockett was busking in New York City, honing his performance skills and eventually forming the street band the Trainrobbers.

2015: First Album Release

In 2015, Charley Crockett began his career with the release of his first album.

2015: Release of A Stolen Jewel and Dallas Observer Music Award

In 2015, Charley Crockett returned to Texas, settled in Dallas, and self-released his debut album, A Stolen Jewel, in May, earning him the Dallas Observer Music Award for Best Blues Act.

2016: Release of In The Night

In 2016, Charley Crockett released a blues-dominated album, In The Night, featuring original songs and covers of Freddy Fender's "Wasted Days and Wasted Nights" and Jerry Lee Lewis' "What's Made Milwaukee Famous".

2017: Release of Lil G.L.'s Honky Tonk Jubilee

In 2017, Charley Crockett released Lil G.L.'s Honky Tonk Jubilee, a collection of covers of country songs, on Thirty Tigers, featuring tracks originally recorded by Roy Acuff, Tanya Tucker, Hank Williams, Ernest Tubb, Loretta Lynn, and Webb Pierce.

2018: Release of Lonesome as a Shadow and Touring

In 2018, Charley Crockett released Lonesome as a Shadow, an album of original songs dedicated to Henry "Ragtime Texas" Thomas, and subsequently toured with his band the Blue Drifters, playing at various venues and festivals.

2018: Release of Lil G.L.'s Blue Bonanza

In late 2018, Charley Crockett released Lil G.L.'s Blue Bonanza, another compilation of cover versions, peaking at number 10 in the Billboard Blues Albums chart.

September 20, 2019: Release of The Valley

On September 20, 2019, Charley Crockett released The Valley, which included the single "Borrowed Time" co-written with Evan Felker of Turnpike Troubadours.

April 3, 2020: Release of Field Recordings, Vol. 1

On April 3, 2020, Charley Crockett released Field Recordings, Vol. 1, a mixtape of 30 low-fidelity covers and originals recorded in Mendocino County, California.

July 31, 2020: Release of Welcome to Hard Times

On July 31, 2020, Charley Crockett released his seventh album, Welcome to Hard Times, produced by Mark Neill with songwriting contributions from Dan Auerbach and Pat McLaughlin, following a health scare and heart surgery.

February 26, 2021: Release of 10 For Slim: Charley Crockett Sings James Hand

On February 26, 2021, Charley Crockett released 10 For Slim: Charley Crockett Sings James Hand, a tribute album to James "Slim" Hand, which received critical acclaim.

September 17, 2021: Release of Music City USA

On September 17, 2021, Charley Crockett released his ninth album, Music City USA, via Son of Davy/Thirty Tigers. The lead single, "I Need Your Love", gained recognition.

March 2022: Announcement of Jukebox Charley

In March 2022, Charley Crockett announced Jukebox Charley, a new album of cover songs.

September 2022: Release of The Man from Waco

In September 2022, Charley Crockett released his 11th album, The Man from Waco, featuring 14 original songs.

November 14, 2022: Recording of Live from the Ryman

On November 14, 2022, Charley Crockett's sold-out headline debut at Nashville's Ryman Auditorium was recorded and would later be released as an album and concert film called Live from the Ryman.

2022: The Man from Waco Album Breaks into US Billboard 200

In 2022, Charley Crockett's album, The Man from Waco, broke into the US Billboard 200.

July 2024: Release of Visions of Dallas

In July 2024, Charley Crockett released Visions of Dallas, an album of six cover songs and six originals, which was billed as chapter two to $10 Cowboy.